Abstract A multistep synthesis of novel pyrene-based thiazole moiety been has been realized following some synthetic challenges and complications. The chemical structure of the synthesized compound has been established on the basis of both spectroscopic and analytical tools. Its nucleophilic reactivity with 4,6-dinitrobenzofuroxan (DNBF) has been successfully studied in solution. A kinetic study of the covalent electrophile/nucleophile combination of dinitrobenzofuroxan (DNBF, electrophile) and 4-(pyren-1-yl)thiazol-2-amine (nucleophile) resulting in the formation of the corresponding σ-adduct in solution is reported. The rate constant (k1) of the second-order relating to the C C bond forming step of this complexation process has been found to fit into the linear correlation log k = sN (N + E), thereby permitting the evaluation of the nucleophilicity parameter (N) of the 4-(pyren-1-yl)thiazol-2-amine. 4-(Pyren-1-yl)thiazol-2-amine has been subsequently ranked according to its reactivity profile on the general nucleophilicity scale developed recently by Mayr et al., leading to an interesting and direct comparison over a large domain of π-, σ-, and n-nucleophiles.

中文翻译：

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亲核性和溶剂对 4-(pyren-1-yl)thiazol-2-amine 与 4,6-dinitrobenzofuroxan 相互作用动力学的影响

摘要 在一些合成挑战和复杂性之后，已经实现了新型芘基噻唑部分的多步合成。合成化合物的化学结构是在光谱和分析工具的基础上确定的。已在溶液中成功研究了其与 4,6-二硝基苯并呋喃 (DNBF) 的亲核反应性。对二硝基苯并呋喃（DNBF，亲电试剂）和 4-（芘-1-基）噻唑-2-胺（亲核试剂）的共价亲电试剂/亲核试剂组合进行动力学研究，导致在溶液中形成相应的 σ-加合物。已发现与该络合过程的 CC 键形成步骤相关的二阶速率常数 (k1) 符合线性相关性 log k = sN (N + E)，从而允许评估 4-(芘-1-基)噻唑-2-胺的亲核性参数 (N)。4-(Pyren-1-yl)thiazol-2-amine 随后根据其在 Mayr 等人最近开发的一般亲核性尺度上的反应性特征进行了排序，从而对大范围的 π- 进行了有趣且直接的比较、σ- 和 n-亲核试剂。